The field of the invention is shaped or unshaped synthetic resin compositions containing quadratic acid amide stabilizers.
The present invention relates to the use of bisamides of quadratic acid as stabilizers for selected shaped or unshaped synthetic resins where the bisamides have the general Formulas I and/or II as follows: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4, are identical or different, and represent
(A) hydrogen, unsubstituted or substituted alkyl or alkenyl residues of 1-22 carbon atoms, one or more of which can also be substituted by hetero atoms;
(B) unsubstituted or substituted cycloalkyl or cycloalkylalkylene residues;
(C) unsubstituted or substituted aryl and arylalkylene residues;
(D) 3- to 8-membered, unsubstituted or substituted rings which contain one or more hetero atoms and which can optionally be connected to the nitrogen atoms of Formulae I and II by way of alkylene groups;
(E) furthermore the groups --NR.sub.1 R.sub.2 and/or --NR.sub.3 R.sub.4 represent 3- to 8-membered, unsubstituted or substituted rings which optionally contain additional hetero atoms; and
(F) respectively R.sub.1 and R.sub.3 or R.sub.2 and R.sub.4 represent unbranched or branched, ring-anellated, saturated or unsaturated aliphatic chains which optionally carry functional groups.
The bisamides are prepared in accordance with conventional methods (e.g. "Angew. Chemie" [Applied Chemistry] 77 [1965] :680; 78 [1966]:927; 80 [1968]: 541; Tetrahedron Letters 1968 : 1339, 1969 : 4115; "Chem. Ber." [Chemical Reports] 103 [1970]: 3553; "Liebigs Ann. Chem. " [Liebig's Annals of Chemistry]1973 : 619) and the 1,2 bisamides of Formula II are prepared as disclosed in British Patent No. 1,186,096; French Patent No. 1,531,943 and German Published Application No. 1,669,798 the disclosures of which are included herein.
The selected shaped or unshaped synthetic resins include homo- and copolymers of olefins or diolefins, e.g. polyisoprene, polybutene, polypropylene, polyethylene of low and high density, polybutadiene, or saturated or unsaturated ethylene-propylene copolymers, ethylene-butene copolymers, ethylene-vinyl acetate copolymers, butadiene-styrene copolymers, butadiene-styrene-acrylonitrile copolymers, furthermore homo- and copolymers of styrene or its homologs, such as .alpha. methylstyrene, e.g. polystyrene, styrene butadiene copolymers, or so-called impact-resistant polystyrene types, such as graft polymers of styrene with elastomers or also mixtures of homo- or copolymers or graft polymers, and furthermore homo- and copolymers and graft polymers of vinyl chloride, such as polyvinyl chloride, polyvinylidene chloride, vinyl chloride-vinylidene chloride copolymers, vinyl chloride-vinyl acetate copolymers, or also polyvinyl acetate, polyether esters, or also polyurethanes, polyisocyanurates, polyacrylonitrile and the copolymers thereof, polyester amides and polyether ester amides.
Especially suitable synthetic resins are polyamides, for example homopolyamides, as they are produced in the usual way from lactams of more than 5 carbon atoms in the ring and/or from the corresponding .omega. amino acids, such as caprolactam, capryllactam, lauryllactam, undecyllactam, enantholactam, or from .omega.,.omega.'-diamines and .omega., .omega.'-dicarboxylic acids of more than 3 carbon atoms between the functional groups, such as, for example, tetramethylenediamine, hexamethylenediamine, trimethylhexamethylenediamine, isophoronediamine, octamethylenediamine, dodecamethylenediamine, and adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedicarboxylic acid, dodecanedicarboxylic acid terephthalic acid, isophthalic acid, and furthermore the corresponding copolyamides and polyether amides. The homo- or copolyamides of lauryllactam are preferably utilized.
The polyester amides suitable as the synthetic resins in the present application are conventionally produced from low-molecular starting components, for example amino alcohols, lactones, diols, dicarboxylic acids, aminocarboxylic acids, lactams, and diamines, or by reactions between polyamides and polyesters (Polyamides ethers than Nylons 6 and 6, 6, part II, Stanford Research Institute, Nov. 1974, pp. 417-422). An especially advantageous process is described in German Published Application No. 2,542,467.
The polyether ester amides contain, as compared to the polyester amides, additionally ether groupings besides the ester and amino groups. The manufacture of polyether ester amides has been described, inter alia, in German Published Applications Nos. 2,523,991 and 2,527,885; and especially advantageous process is suggested in German Published Application No. 2,712,987. The particularly advantageous mixtures of polyether ester amides and polyamides are proposed in German Published Application No. 2,716,004.
The mechanical properties of synthetic resins are, as is known, extensively impaired by the effects of elevated temperatures, oxygen, and light radiation. Numerous substances have become known as stabilizers for synthetic resins (Thinius, "Stabilisierung und Alterung von Plastwerkstoffen" [Stabilization and Aging of Synthetic Resins] vol. 1: 167-634 [1969]).
The conventional stabilizers do not achieve the desired, broad spectrum of application so that in each case specifically chosen stabilizer systems must be utilized for the various synthetic resins. However, even within an individual class of synthetic resins, it is necessary to use a great variety of different stabilizer mixtures depending on the type of stabilization desired.
It is known from German Published Application No. 1,669,798 to employ, inter alia, 1,2-bisamides of quadratic acid as stabilizers against oxidative or thermaloxidative degradation of polyacetals.